Miles of Smiles: The Best Midwest Road Trip Routes
Discover the best Midwest road trip routes, featuring scenic drives and small towns, in this easy guide to exploring America's heartland.
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Have you ever felt the thrill of hitting the open road with nothing but the horizon ahead? If you’re dreaming of a road trip adventure through the Midwest of America, you’re in for a treat! As a travel blogger who’s roamed these routes extensively, I’m excited to share some of the best Midwest road trip routes that will guarantee you miles of smiles.
From the iconic Route 66 to the Great River Road, the Midwest is packed with incredible journeys that promise both adventure and relaxation. I’ve personally explored many of these destinations and discovered countless hidden gems along the way.
Whether you’re craving the excitement of big cities or the serenity of scenic drives, this guide will help you navigate the best road trips in the Midwest. Buckle up because these routes are filled with adventures that will keep you smiling from start to finish!
Before diving right in, here’s one quick, but very important tip! Always get reliable travel insurance when planning for any solo adventure. I recommend SafetyWing. Their flexible policies cover incidents in over 185 countries, and I don’t need to provide a travel itinerary in advance. In fact, you can sign up for SafetyWing even if you’re already on the go.
Route 66
Route 66, known as the "Main Street of America," is a legendary highway that spans over 2,400 miles from Chicago, Illinois, to Santa Monica, California. While it crosses the entire country, the Midwest section is where the road's authentic charm shines, offering some of the best stops and scenery.
The journey begins in Chicago, Illinois, with landmarks like the famous Lou Mitchell’s diner. As you head through Illinois, the road takes you to small towns like Joliet and Pontiac, where you can explore the Route 66 Hall of Fame and Museum and see quirky roadside attractions like the Gemini Giant.
In Missouri, Route 66 passes through St. Louis, where you can visit the Gateway Arch and enjoy local barbecue. As the road winds through the Ozarks, you’ll find old-school motels and the Route 66 Car Museum in Springfield.
Though Kansas has the shortest stretch of Route 66, it’s full of history. The small town of Galena offers a look back at the road’s early days with vintage service stations and classic Americana charm.
In Oklahoma, the route takes you through Tulsa and Oklahoma City, where you can explore Art Deco buildings and visit the National Cowboy & Western Heritage Museum. Don’t miss the Round Barn in Arcadia or the milk bottle building in Oklahoma City, which are both unique stops along the way.
Great Lakes Circle Tour
The Great Lakes Circle Tour is an incredible road trip that takes you around the shores of Lake Michigan, Huron, Erie, and Ontario. This scenic route offers great views, cool cities, and small towns as you explore the heart of the Great Lakes region.
Starting in Chicago, Illinois, you can enjoy the city’s skyline along Lake Michigan, visit Navy Pier, and stroll through Millennium Park. As you drive north along Lake Michigan, you’ll pass through towns like Milwaukee, Wisconsin, and Traverse City, Michigan, known for their beautiful beaches and outdoor activities.
Crossing over to Lake Huron, the tour takes you through the Upper Peninsula of Michigan, where you can explore Mackinac Island, famous for its historic charm and fudge shops. Continue along the shores of Lake Huron, passing through quaint towns and enjoying the peaceful, scenic drives.
Heading south, Detroit, Michigan, awaits with its automotive history, cultural scene, and waterfront along the Detroit River. From there, the route takes you along Lake Erie, where you can stop in Cleveland, Ohio, home to the Rock and Roll Hall of Fame and lively entertainment districts.
Bonus: If you have a passport and the extra time, consider crossing into Canada! The tour brings you to Toronto, Ontario, where you can experience the city’s neighborhoods, visit the iconic CN Tower, and explore the beautiful Toronto Islands. The journey continues along the northern shores of Lake Ontario, offering more views and opportunities to explore Canadian culture.
Great River Road
The Great River Road is an epic road trip that follows the Mississippi River from its source in Minnesota all the way to the Gulf of Mexico. As you journey along this route, you’ll pass through ten states and history tied to America’s greatest river.
Starting at the headwaters in Minnesota, the road begins in Itasca State Park, where you can see the very start of the Mississippi River. As you travel south, you’ll pass through river towns like Red Wing and Winona.
In Wisconsin and Iowa, the Great River Road winds through scenic byways with rolling hills, forests, and river views. Towns like La Crosse, Wisconsin, and Dubuque, Iowa, offer cultural experiences and museums that tell the story of the Mississippi’s impact on the region.
Moving into Illinois and Missouri, the route takes you through larger cities like St. Louis, Missouri, where you can visit the iconic Gateway Arch and learn about the river’s role in westward expansion.
As you continue south, Tennessee offers a blend of beauty and Southern hospitality. In Memphis, you can visit Graceland, explore Beale Street’s lively music scene, and learn about the river’s influence on the city’s blues and rock ‘n’ roll.
Crossing into Arkansas and Mississippi, the landscape shifts to the rich delta region, known for its culture, soulful music, and delicious food. The Great River Road takes you through historic plantations, bayous, and wetlands.
Finally, the road reaches its end in New Orleans, Louisiana, where the Mississippi River flows into the Gulf of Mexico. In New Orleans, you can experience the French Quarter, enjoy live jazz, and see for yourself why it’s one of my favorite cities in the world!
Click here for some of the best tours along the way!
Midwest Metropolis Tour
The Midwest Metropolis Tour is a road trip that takes you through some of the most dynamic cities in the heart of America: Chicago, Detroit, Minneapolis, and St. Louis.
The tour starts in Chicago, Illinois, in the Windy City, where you can see the stunning skyline along Lake Michigan, visit the Art Institute of Chicago, and explore Millennium Park. Don’t miss the chance to take a boat tour along the Chicago River, where you’ll see some of the most iconic buildings in the world and see great sunsets.
Next, head to Detroit, Michigan, a city that’s undergone a remarkable transformation in recent years. Here, you can explore the Detroit Institute of Arts, known for the famous Diego Rivera murals. The city’s downtown offers trendy restaurants, lively music venues, and the Motown Museum, where you can see the roots of American music.
Continuing on to Minneapolis, Minnesota, you’ll find a city that blends beauty with urban sophistication. Visit the Walker Art Center, home to contemporary art and the famous Minneapolis Sculpture Garden, where the Spoonbridge and Cherry sculpture has become a city icon. The nearby Chain of Lakes offers a perfect escape within the city for biking, walking, or enjoying the outdoors.
Finally, the tour takes you to St. Louis, Missouri, where the Gateway Arch stands as a symbol of the city’s role in America’s westward expansion. Don’t forget to try some St. Louis-style barbecue and take a riverboat cruise on the Mississippi River.
Click here for some of the best tours along the way!
Ohio River Valley
The Ohio River Valley road trip takes you through the culture of Ohio, Kentucky, Indiana, and West Virginia along the Ohio River.
Starting in Cincinnati, Ohio, the journey begins in the "Queen City," where you can see Smale Riverfront Park, explore the National Underground Railroad Freedom Center, and wander around the Over-the-Rhine district. Cincinnati is also known for its food scene, so be sure to try the city’s famous chili.
Next, head to Louisville, Kentucky, home of the Kentucky Derby and rich in Southern charm. Visit the historic Churchill Downs, tour the Louisville Slugger Museum & Factory, and explore the arts scene in the NuLu district. Don’t miss a stop at the Muhammad Ali Center, dedicated to the life and legacy of the boxing legend.
In Indiana, the Ohio River Valley takes you through river towns like Madison, known for its well-preserved historic district and views along the river. Here, you can step back in time as you explore 19th-century homes and Clifty Falls State Park.
Crossing into West Virginia, the road trip continues to Pittsburgh, Pennsylvania, where the Ohio River meets the Allegheny and Monongahela Rivers. Pittsburgh, once known for its steel industry, has reinvented itself as a hub for technology, culture, and the arts. Visit the Andy Warhol Museum, explore the Carnegie Museum of Art and Natural History, and take in views of the city from Mount Washington.
Click here for some of the best tours along the way!
Great Smoky Mountains and Blue Ridge Parkway
The Great Smoky Mountains and Blue Ridge Parkway road trip takes you through some of the most scenic landscapes in Tennessee and North Carolina.
The route starts in Gatlinburg, Tennessee, and is the gateway to the Great Smoky Mountains National Park. Hike the famous Alum Cave Trail for panoramic views, or visit Cades Cove to see buildings and wildlife. Gatlinburg itself is a charming town with plenty of attractions, so be sure to book a cabin for a night or two!
As you travel along the Great Smoky Mountains National Park, you’ll experience some of the park’s best sights. Take the scenic drive along Newfound Gap Road for spectacular mountain vistas, and stop at Clingmans Dome, the highest point in the park, for breathtaking 360-degree views.
Moving into North Carolina, the route joins the Blue Ridge Parkway, known for its beauty and recreational opportunities. Begin in Asheville, explore the Biltmore Estate, America’s largest privately owned home, and wander through the River Arts District. If you visit in the fall, be ready for a beautiful drive as the leaves change colors!
The Blue Ridge Parkway stretches through North Carolina with countless overlooks and hiking trails. Visit the Linn Cove Viaduct and hike to Linville Falls for views of the waterfall and the surrounding gorge. The parkway also offers access to towns like Blowing Rock and Boone, where you can enjoy local shops, restaurants, and cozy accommodations.
Lake Michigan Shore
The Lake Michigan Shore road trip offers a journey along the coastline of Lake Michigan, exploring the beaches, dunes, and towns of Indiana and Michigan. This route provides a perfect blend of outdoor adventures and picturesque stops.
Starting in Indiana, the journey begins at the Indiana Dunes National Park, where you can explore miles of sandy beaches and scenic dunes. The park features over 15 miles of Lake Michigan shoreline, ideal for swimming, picnicking, and hiking.
As you continue north, you’ll enter Michigan, where the Lake Michigan Shore truly shines. In South Haven, you can enjoy the historic lighthouse and sandy beaches. Don’t miss a visit to the local wineries and orchards in the area, which offer a taste of Michigan’s agriculture.
Further along the coast, Saugatuck is known for its artsy vibe and Oval Beach. The town offers a variety of galleries, boutiques, and restaurants, making it a great spot to relax and soak in the views.
In Holland, you’ll find a blend of Dutch heritage and modern charm. Visit the Windmill Island Gardens, explore the Holland Harbor Lighthouse, and enjoy the local festivals and events. The town’s downtown area is full of shops and restaurants that reflect its Dutch roots.
Finally, the road trip concludes in Muskegon, where you can explore the scenic Muskegon State Park, offering expansive beaches and wooded trails. Plus, the city’s waterfront area features a boardwalk and a variety of recreational activities, including boating and fishing.
Click here for some of the best tours along the way!
Iowa's Loess Hills
Finally, the Iowa's Loess Hills road trip offers an adventure through one of Iowa’s most unique landscapes, characterized by its rolling hills and small towns.
Starting in Council Bluffs, Iowa, the journey begins in a city with a history and views of the Loess Hills. Explore the Union Pacific Railroad Museum and take a stroll through the Lake Manawa State Park.
As you drive through the Loess Hills region, you'll encounter Glenwood, a charming town known for its downtown, and the Glenwood Archaeological Site. The site features ancient Native American earthworks and offers a glimpse into the area’s history.
Continuing north, visit Woodbine, where you can enjoy the town’s Main Street and historic buildings. In Onawa, explore the Loess Hills Scenic Byway and take in the sweeping views of the rolling hills.
Further along the route, make a stop in Sioux City, where you can explore attractions like the Sioux City Art Center and the Sioux City Public Museum. The city’s downtown area offers a variety of dining and shopping options to complete your trip.
I hope this guide has helped you with planning your ultimate road trip adventure across the Midwest! If you decide to set off on the open road on one of these Midwest road trips, you’re in for a fantastic adventure; be sure to let me know how it goes!